3,3'-Bicarbazole

CAS Number 1984-49-2

Chemistry Building Blocks, Heterocyclic Building Blocks, Monomers

3,3'-Bicarbazole, Bicarbazole derivative

A useful building block for the synthesis of hole transport layer, host, TADF emitting layer materials in application of organic light-emitting devices and perovskite solar cells.

Overview
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3,3'-Bicarbazole (CAS number 1984-49-2) is a bicarbazole derivate that is formed by joining two carbazole units at 3,3'-positions. Bonding at 3,3'-positions not only extends the conjugation of each individual carbazole units but also improves the stability by partially blocking the electron active sites at 3,3'-positions.

As a bipolar charge transporting material derived from 3,3‘-bicarbazole, triphenylsilyl-substituted 3,3‘-bicarbazole, was found to be a good phosphorescent host that is competitive with the widely used host mCP. Warm-white-emissive device exploring 9-(9,9’-spirobi[fluoren]-3-yl)-9’-phenyl-9H,9’H-3,3’-bicarbazole (SFBCz) as one of the exciplex-forming hosts, a blue TADF-sensitizer 5TCzBN, and a yellow fluorescent dopant TBRb in a single-emissive-layer demonstrated an external quantum efficiency of 21.4%, a benchmark PE of 69.6 lm W^-1, and a remarkable T80 of >8200 h at 1000 cd m^-2.

Highly efficient and stable perovskite solar cells using the p–i–n device structure ITO/NiOx/NP-BC/perovskite/PC61BM/BCP/Ag achieved an overall PCE of almost 20%. NP-BC is 3,3′-bicarbazole-based hole transporting material 9,9'-Diphenyl-9H,9'H-3,3'-bicarbazole, also named as BczPh.

General Information

CAS Number	1984-49-2
Chemical Formula	C₂₄H₁₆N₂
Molecular Weight	332.41 g/mol
Full Name	3,3'-Bicarbazole
Synonyms	9H,9'H-3,3'-Bicarbazole, 3,3'-Bi-9H-carbazole; 9H,9H-[3,3]Bicarbazolyl
Classification / Family	Bicarbazole derivatives, Semiconductor synthesis intermediates, Heterocyclic building blocks

Chemical Structure

Product Details

Purity	>98% (¹H NMR)
Melting Point	N/A
Appearance	Off-white to grey powder/crystals

MSDS Documentation

3,3'-Bicarbazole MSDS Sheet

Literature and Reviews

3,3′-Bicarbazole-based compounds as bipolar hosts for green and red phosphorescent organic light-emitting devices, O. Bezvikonnyi et al., Mater. Sci. Eng. B, 261, 114662 (2020); DOI: 10.1016/j.mseb.2020.114662.
Forming a Metal-Free Oxidatively Coupled Agent, Bicarbazole, as a Defect Passivation for HTM and an Interfacial Layer in a p–i–n Perovskite Solar Cell Exhibits Nearly 20% Efficiency, S. Maddala et al., Chem. Mater., 32 (1), 127–138 (2020); DOI: 10.1021/acs.chemmater.9b02720.
A π–D and π–A Exciplex-Forming Host for High-Efficiency and Long-Lifetime Single-Emissive-Layer Fluorescent White Organic Light-Emitting Diodes, C. Zhang et al., Adv. Mater., 32 (42), 2004040 (2020); DOI: 10.1002/adma.202004040.
Revealing the Cooperative Relationship between Spin, Energy, and Polarization Parameters toward Developing High-Efficiency Exciplex Light-Emitting Diodes, M. Wang et al., Adv. Mater., 31 (46), 1904114 (2019); DOI: 10.1002/adma.201904114.
A thermally cross-linkable hole-transporting small-molecule for efficient solution-processed organic light emitting diodes, D. Dubey et al., Org. Electron., 73, 94-101 (2019); DOI: 10.1016/j.orgel.2019.06.011.
High Fluorescence Rate of Thermally Activated Delayed Fluorescence Emitters for Efficient and Stable Blue OLEDs, L. Su et al., ACS Appl. Mater. Interfaces, 12 (28), 31706–31715 (2020); DOI: 10.1021/acsami.0c07840.

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